Account Executive - Healthcare IT Managed Services

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Account Executive - Healthcare IT Managed Services

Account Executive - Healthcare IT Managed Services
Fully Remote Remote Worker - N/A

Do you love the thrill of a cold call that turns into a real conversation with a CEO? Five Nines is looking for a disciplined, high-activity Account Executive to build new business with hospitals, health systems, and clinics across the United States. You'll spend a big part of every week on the phone opening doors with executives who have never heard of us, then own those opportunities all the way to a signed agreement.

If you handle rejection well, run your own pipeline, and want uncapped upside backed by a nationally recognized brand, this is your territory. Are you in?

• Own your territory. Build and work your own plan targeting hospitals, health systems, and clinics of roughly 50 to 250 employees across the U.S.
• Hit the phones with a head start. You'll start with a curated, vetted prospect list and a proven call script, then make 300 cold calls a week, backed by email outreach, to open conversations with executives who don't know us yet.
• Fill your calendar. Turn that outreach into at least two first meetings a week with qualified decision makers.
• Run the whole deal. Take every opportunity from first call through discovery, proposal, negotiation, and signed agreement.
• Sit across from the C‑suite. Build relationships with CEOs, CFOs, COOs, administrators, and practice administrators, and position Five Nines as their partner in security, compliance, and operational continuity.
• Get sharper every week. Receive specific coaching on your own calls through our proprietary revenue intelligence and call coaching systems.
• Win in the room. Deliver tailored presentations and proposals to executive audiences and contribute to RFP responses.
• Be the face of Five Nines. Represent us at regional and national healthcare association events and keep your pipeline and forecast sharp in Hub Spot.

• 3+ years of B2B sales experience with a proven record of meeting or exceeding quota.
• Demonstrated success building pipeline through high-volume cold calling and proactive outbound outreach.
• Comfort engaging C-level executives and leading business-level conversations.
• Ability to explain technology concepts in plain, non-technical terms.
• Self-motivated and able to execute a territory plan without heavy oversight.
• Experience with a CRM (Hub Spot preferred).
• Willingness to travel up to 20%, primarily for industry events and select client meetings.

• IT managed services or technology sales experience.
• Knowledge of the healthcare industry, including how hospitals and clinics operate and buy.
• Familiarity with HIPAA or other healthcare compliance requirements.

• Big earning potential: Competitive base salary plus uncapped commission, with clear OTE goals of $100K to $150K+.
• A clear path up: Defined routes into sales leadership, supported by mentorship and job shadowing.
• Benefits that matter: High-quality medical, dental, and vision coverage, telemedicine, EAP, and a 401(k) with company match.
• Time to recharge: Open PTO and paid holidays.
• Flexibility: Work remotely or hybrid, with the independence to manage your own week.